As we enter Black History Month in the USA, Sydney Montgomery, a graduate of Princeton and Harvard Law School and an admissions consultant, shares how she is helping students from diverse backgrounds to aspire to America’s Ivy League and top law schools. Here she reveals the barriers that Black students face and why acknowledging the existence of racism is crucial for achieving equality.

Dismantling systemic racism depends on people “not being afraid to ruffle feathers,” otherwise fear just leads to continuing acceptance of inequality.

Sydney Montgomery argues that just acknowledging that racism is an issue is an important first step in achieving change. As founder of an admissions consulting service, she aims to level the higher education playing field in the US to enable more students from minority and poorer backgrounds to enter top universities and law schools. 

And, with an impressive degree of success. The key to Montgomery’s strategy is helping Black students prepare the essays they need to submit in the admissions process. In 2017 78% of applicants who benefitted from Montgomery’s services got into law school, compared with 51% for the US as a whole.

“I consider myself an essay specialist,” she says proudly. “A lot of students have trouble organising their thoughts because maybe they haven’t been taught how due to their educational backgrounds. I go through a very specific process of brainstorming, organising, structuring and drafting the essays.”

Montgomery also runs boot camps, which have proved particularly helpful for ‘first-generation students because they encourage community and accountability. Organising them in groups of three or four students has led to higher success rates – 91% of her students admitted to law school were first-generation or from a minority.

All her aspiring law school students are assigned a mentor recruited from Harvard Law School, clients and friends. While Montgomery specialises in law school admissions, she also helps high school pupils with their college applications. They, too, are given mentors.

“What makes me a little different from other consulting firms is that I don’t believe it’s a transactional process – it’s relational,” says Montgomery. “My business is partially faith-based. I cannot tell you the number of times I tell my students to text me if they have a bad day.

“We will often get on the phone and pray together. I also lead prayer groups on Facebook group and YouTube. I strongly believe in taking a moment to see people as people. I’m a big advocate for mental health resources, and I’ve recommended some of my students get therapy.”

Ivy League should attract more Black students

Montgomery’s journey through higher education, first Princeton University and then Harvard Law School, is what inspired her to help others. Although her parents had degrees, they acquired them while enlisted in the military, which meant they were unfamiliar with the traditional applications process.

“That’s where some of those difficulties for me came,” Montgomery recalls. “I had teachers that really stepped in to help me. But there are many things that I wouldn’t have done if I’d had someone like myself to guide me. I didn’t know that I was Ivy League material or know anyone who had ever gone to an Ivy League school. The scariest thing for me was not knowing where I stood against other students.”

Montgomery co-produced the College Equity Index, which evaluates spaces created for Black students and rates colleges accordingly. She believes that Ivy League colleges could encourage Black students by having representatives from diverse backgrounds at their admissions information sessions. She argues that employing Black admissions officers, directors, and front-facing staff would make students from diverse backgrounds feel less like they were there to fulfil a quota.

The US could learn from Canada, which has separate applications for people from historically underrepresented or disadvantaged groups. “We don’t do much like this here [in the US],” Montgomery explains. “We have some programmes, like QuestBridge, which are looking for exceptionally highly gifted, but also incredibly low-income students. Those programmes are fantastic and do a lot of good. But we’re still missing a large swathe who could benefit from schools having a different look at students from certain backgrounds. Affirmative action is still hotly debated on so many levels.”

Financial support

There was also the issue of financial support. Those from wealthy backgrounds were more able to engage in various extracurricular activities, such as debate teams, cheerleading or running non-profits. In contrast, poorer students often had to take part-time jobs to make ends meet.  

While there is financial support to help the less well-off – need-based aid based on the family’s financial situation and merit-based aid – Montgomery reveals that less than 100 schools in the US meet ‘demonstrated need’ and offer financial support.

“But some of that is still loans,” she points out. “Very few schools are going to meet 100% of your need without loans, meaning they will give you grants for it. On the flip side, some schools only give merit aid because they’re only using their aid dollars to attract top talent, and they don’t meet a lot of demonstrated need.”

It was at Harvard Law School that Montgomery started to help other Black students, and what gave her the impetus to change course. “I took stock of the fact that there were so many little things that led to me being here,” she says. “But, if those little things had been slightly different, I might have ended up somewhere else. And I started looking at the profession of admissions.”

Think in Color

She set up S. Montgomery Admissions Consulting part-time, joined professional associations and got the relevant training while, at the same time, practising family law litigation. Then, in 2020, after hearing the experiences of women entrepreneurs at the Think in Color Summit, she decided to expand her business full-time.

“I had never seen so many women entrepreneurs of colour in the digital space,” Montgomery reveals. “I had read all these books, by mostly White men, saying how you had to have six to 12 months of savings before you were doing anything. So, I assumed I couldn’t be an entrepreneur because I didn’t have savings.

“I was on podcasts talking about equity in law school admissions and how consultants can dismantle systemic racism. Someone told me they’d never seen a Black woman consultant before in law school admissions and that they’d been searching for a woman of colour to help them for months. Think in Color inspired me to say I can do this full time and helped make that plan into fruition.”

As a member of the Board of Advisors to the Institute for Anti-Racist Education, Montgomery also devotes her time to dismantling systemic racism in education. She cites the example of Michelle Obama, who was told by her school counsellor not to apply to Princeton. Often black students, especially when changing schools, would not be placed on the courses that would help them succeed, affecting their college applications. Also, whereas White students were asked about their greatest skill or accomplishment, their Black counterparts were asked to focus on how they overcame a traumatic experience.

The Institute works with individual teachers on their own racial journey and on understanding how they are conveying that to students in class. Montgomery has pushed the Independent Educational Consultants Association to make cultural competency training mandatory. This would ensure that admissions consultants would be fully equipped to deal with the students they were trying to help.

Dismantling systemic racism

Montgomery admits that dismantling systemic racism would take time, and the first hurdle was accepting that it was a reality. “When we look at the history of education in this country, Black people were not encouraged to be literate,” she says. “When they did make schools, they were burned down, and teachers were lynched. There were several active campaigns to disrupt the education of Black students, even when we were trying to educate ourselves.

“In a lot of those areas, education is still depressed. Private schools are one of the largest forces for segregation. More students going to private schools is just a way to keep the public school system in a depressed and stagnant state. So, even before we get to the college admissions process, the quality of education that students are getting is not equal.

“America has had a terrible time agreeing to facts. Every state gets to teach history in its own way. And certain states don’t like to teach history the correct way. But we can’t make progress on dismantling racism without agreeing that racism exists. And right now, there’s this debate about critical race theory, which is not what they say it is. It’s a very specific thing, but they’re using it as a caveat to say we don’t want race and racism taught in schools. We don’t want it taught in universities.

“Realistically, we can create change by holding people who are in power accountable. Some schools have done reparations for slavery; Georgetown is one of them. Princeton Theological Seminary is another one. Presidents at private schools can set the course for how their school will address their wrongs and what their school will teach. While that may be harder for some public schools, not being afraid to ruffle feathers is the first way to dismantle systemic racism. Because when people are afraid to ruffle feathers, they’re really saying they’re okay with the fact that some people are still going to be oppressed.”

Inclusive environment

Montgomery’s consultancy’s success in helping Black and minority students to get into law schools has meant that the business has expanded rapidly. She takes her responsibilities as a leader seriously and works hard to provide an inclusive environment for her eight-strong team.

“I found this fantastic employee management software called 15 Five,” she says. “We do weekly check-ins or bi-weekly one on ones. We ask qualitative questions about ‘how are you feeling’? ‘What are you struggling with’? ‘Where did you find joy in your work this week’?

“Having a remote team is a little challenging, but I have been intentional about having weekly team meetings, about doing some happy hours to create the collaboration, because we are stronger together. Instead of just saying, ‘I need you to work a certain way’, I try to say ‘how do you best work’? And then how can we make that work for the team? I’ve found that has really helped make sure that everyone feels supported and included.”

Turning to the legal world, she argues that more discussion is needed to address the issues that Black women face. Also, while there were more women in law schools than men, fewer made it to partner level. There was the added discrepancy of women tending to go to lower-ranked law schools with lower bar pass rates. Also, they tended to borrow more, creating an added financial burden. 

Montgomery suggests that law firms should offer more pipeline programmes because “the cost of applying to law school is tremendous – anywhere from $1,300 to $4,000. Some firms will give you summer employment. Getting to that firm culture early, before you even start school or knowing that you have a place to go after school, really helps.”

As a keynote speaker at last summer’s Think in Color Summit, Montgomery was pleased to demonstrate and inspire other women that it was possible to become an entrepreneur outside the traditional mould.

Finally, she adds: “I’ve been able to find my voice, also within a faith-based context, despite always being told that business and faith need to be separate. I think more people can unashamedly not be afraid to be who they are and live confidently in their truth and authenticity.

“I will forever empower women of colour to entrepreneurship or higher education because we still need that representation for people to know that they can achieve their dreams.”